Frequently Asked
Questions

Yes! Check Cherry offers a 14-day free trial with full access to all features. No credit card required to start.

Start your free trial

Absolutely. Check Cherry integrates with any website—WordPress, Squarespace, Wix, or custom builds. Simply copy and paste booking links onto your site.

You can link directly to specific packages, your full booking page, or the client portal where customers manage their reservations.

Most users are up and running in under an hour. Add your first package, connect payments, and you're ready to send proposals.

We also offer free onboarding calls if you want a guided walkthrough.

Not at all. If you can use email and social media, you can use Check Cherry. Everything is point-and-click—no coding or technical knowledge required.

Our interface is designed for busy event pros, not IT departments.

Yes! While we don't have a self-service upload tool (every system structures data differently), our team can help import your existing clients. Just export your data from your current system and send us the file—we'll make sure everything maps correctly.

We've done this for many customers coming from a variety of platforms, so you're in good hands.

Check Cherry is available in English and supports the following countries:

Check Cherry plans start at $39/month for solo operators. We offer plans for growing teams and multi-brand businesses too.

See all pricing options

Yes! Pay annually and get 2 months free compared to monthly billing. You can switch between monthly and annual billing anytime from your account settings.

Yes, you can change your plan anytime. Upgrades take effect immediately. Downgrades take effect at your next billing cycle.

There are no penalties or fees for changing plans.

US Customers (Check Cherry Payments)

• 2.9% + 30¢ per successful card charge
• 1.5% for ACH Direct Debit
• Apple Pay and Google Pay supported
• $15 dispute (chargeback) fee
• No setup fees, monthly fees, or hidden fees
• +1% for international cards, +1% if currency conversion required

Outside the US

Connect your existing Stripe account. Processing rates are set by Stripe.

With Check Cherry Payments (US), funds typically arrive in your bank account within 2-3 business days.

Yes! Check Cherry gives you full control over how you get paid:

• Collect deposits (fixed amount or percentage)
• Set up automatic payment schedules
• Send payment reminders automatically
• Accept final payments before the event

You can customize payment terms for each event type or let clients choose their payment schedule.

Yes! If you sell with packages and add-ons, Check Cherry is built for you. Organize your offerings with services, package groups, and individual packages.

We also support multiple brands within one account—perfect if you run a photo booth company and a DJ business, for example.

The client portal is a self-service hub where your clients can manage their booking. They can:

• View and sign contracts
• Make payments
• Complete planning forms and questionnaires
• Select options (like photo booth templates or song requests)
• See event details and timelines

This dramatically reduces back-and-forth emails—clients get answers instantly instead of waiting for you to respond.

Yes! Your booking page is fully customizable:

• Add your logo and brand colors
• Choose which packages to display
• Set your own URL
• Add photos and descriptions
• Control what information you collect

Your clients see a professional, branded experience that matches your business.

Yes! Check Cherry's automation engine lets you send emails and texts automatically based on triggers like:

• New booking confirmed
• Payment reminder (X days before due)
• Planning form reminder
• Event reminder (day before, week before, etc.)
• Post-event follow-up and review requests

Learn more about automation

Check Cherry handles travel fees automatically:

• Set a "free travel" radius from your base location
• Define per-mile rates beyond that radius
• Travel fees calculate automatically when clients enter their venue address
• Clients see the travel fee before they book—no surprises

You can also set flat travel fees for specific zones if you prefer.

Yes. You can block dates directly in Check Cherry so clients can't book when you're unavailable. Blocked dates sync with your calendar integrations too.

This is great for vacations, personal events, or days you're already booked through other channels.

Yes. Check Cherry includes built-in e-signatures. Clients can review and sign contracts from any device, and you'll get notified instantly when they sign.

All signed contracts are stored securely and accessible anytime from your dashboard.

E-signatures through Check Cherry are legally binding and include a complete audit trail (timestamp, IP address, and signer verification).

Absolutely. You can paste your existing contract language into Check Cherry's contract builder. Add merge fields to auto-populate client names, dates, package details, and more.

We also provide starter templates if you need a foundation to work from.

Brands let you display a separate logo, URL, and color scheme to clients—all from one Check Cherry account. Bookings roll up to the same calendar so you see everything in one place.

Watch: How Brands Work

Yes! Check Cherry offers native apps for iOS and Android for staff and admin accounts. We also have a fully responsive web app that works great on any device.

Your clients get a mobile-friendly portal to sign contracts, make payments, and complete planning forms.

Yes! We offer a direct two-way sync with Google Calendar. For other calendars, Check Cherry provides an iCal (.ics) feed that works with Apple Calendar, Outlook, Yahoo Calendar, and any app that supports iCal subscriptions.

Events appear on your personal calendar automatically, keeping everything in sync.

Yes! Our QuickBooks Online integration syncs your invoices and payments automatically. No more double-entry or manual reconciliation.

When a client pays through Check Cherry, the payment is recorded in QuickBooks automatically.

Yes! Check Cherry integrates with Zapier, giving you access to thousands of apps. Popular automations include:

• Add new leads to your email marketing list
• Create Trello cards for new bookings
• Send Slack notifications when contracts are signed
• Update spreadsheets with booking data

If you can dream it up, you can probably automate it.

Yes. Check Cherry integrates directly with Mailchimp. You can also use Zapier to connect with other email platforms like ConvertKit, ActiveCampaign, or Constant Contact.

Automatically add new clients to your mailing list or specific segments based on their booking type.

Yes! Check Cherry's Zoom integration lets you schedule consultation calls. When a client books a meeting, a Zoom link is created automatically and included in confirmation emails.

Perfect for virtual consultations, planning calls, or post-event debriefs.

Yes! All plans include unlimited staff accounts. Staff can be assigned to events, see their own schedules, and access the mobile app. Admin accounts (with full access to settings and reports) have caps based on your plan.

Each person gets their own login and can access the features they need.

Yes. Admins have full access, while staff permissions can be customized per person. You control who sees pricing, who can manage leads and proposals, and who just needs to see their assigned events.

Check Cherry makes staff scheduling simple:

• Assign team members to events
• Staff see their schedule in their own dashboard
• Set staff availability and block-out dates
• Track who's working which events
• Send staff notifications when they're assigned

Learn more about staff scheduling

Yes. With staff-level permissions, team members only see the events they're assigned to. They won't see other bookings, financial details, or client information for events they're not working.

This keeps your business data secure while giving staff what they need.

Yes! We recommend starting with the free trial to get a feel for Check Cherry and make sure it's right for you. Once you're ready, our team can help import your client data.

Most users keep both systems running in parallel for a few weeks, then fully switch over.

Common reasons we hear:

• Modern and polished. Other event software can feel clunky and outdated. Check Cherry is smooth and looks professional to clients.
• Built for events, not generic freelancing. Check Cherry understands packages, add-ons, and event-day logistics.
• Client portal reduces back-and-forth. Clients help themselves instead of emailing you for every update.
• Faster support. Our team typically responds in minutes, not days.

You have a few options for existing bookings:

• Keep them in your old system until they're completed
• Manually create them in Check Cherry for a clean calendar view
• Import basic event info via CSV and add details as needed

Most people run both systems for a bit, then once they get the hang of Check Cherry, they add existing bookings manually via Quick Add or import them with our help.

Multiple ways to reach us:

• Live chat - Click the chat icon anytime (we typically respond in 2-5 minutes during business hours)
• Email - hello@checkcherry.com
• Check Cherry Live - Free training webinars every other Tuesday
• Feature videos - Short tutorials for every feature

Browse feature videos

In-app chat is our primary support channel—it's fast and works great for most questions. But when a call makes more sense, we offer Package Setup, Website Integration, and Account Review calls.

You can schedule directly from your account or chat with us to book a time.

Yes. Check Cherry takes security seriously:

• All data encrypted in transit (SSL/TLS) and at rest
• PCI-DSS compliant payment processing
• Regular security updates and monitoring
• Continuous data backups with point-in-time recovery

We never sell your data or your clients' data.

Yes. E-signatures through Check Cherry are legally binding and include a complete audit trail—timestamp, IP address, and signer verification for every signed document.

Yes. No long-term contracts required. You can cancel your subscription at any time from your account settings.

If you cancel, you'll keep access until the end of your billing period.

Yes. Your data is yours. You can export client lists and event data at any time.

If you need help with an export, just chat with us from your account.